Chicago: What to See and What to Skip

Tourists admire The Cloud Gate, also called the "Bean," sculpture in Millennium Park in Chicago.

Getty Images

My kind of town? Absolutely. Chicago can be a traveler's paradise, with world-class restaurants and bars, music venues and theaters, museums and attractions all within a short stroll from your hotel. But Chicago is, itself, a city of trekkers, with thousands of people traveling from their suburban homes into the heart of the city every day. The Windy City, therefore, might be best defined by venues and attractions well off the beaten path. Here are a few ideas.

See the 'Hoods, Skip the Loop

For tourists, the famous Chicago Loop is the heart of the action: great hotels, great restaurants, great entertainment. But any local will tell you that where a genuine taste of Chicago thrives is in the many unique neighborhoods that radiate out from Chicago's downtown.

Take Pilsen, a neighborhood founded by Eastern Europeans in the late 1800s that is now home to a wonderful enclave of residents of Mexican, if not Hispanic, descent. Richly colorful murals abound, as do authentic eateries and shops, especially along 18th Street. Pilsen is on the National Registry of Historic Places and is home to the must-see National Museum of Mexican Art and the must-visit "2nd Friday Gallery Night," a monthly community event that sees local artists throw open their studio doors.

Of course, more than 75 other wonderful Chicago communities abound, including Lincoln Square to the city's north, home to German bars, approachable restaurants and the great Old Town School of Folk Music, and Lake View, where Boystown, Wrigley Field and the shores of Lake Michigan are all within walking distance.

Ride the 'L,' Skip the Tour

Organized tours can be a great way to learn the ins and outs of an amazing city like Chicago. But the "L," Chicago's rapid transit system, provides eight lines for you to explore the city, and its 'burbs, on your own. The routes are color-themed; the Brown Line takes you into Chicago from the eclectic Albany Park neighborhood, with some dramatic city views as you ride in, while the Blue Line runs 24 hours and is a traffic-free and cheap way to get from O'Hare to downtown. If you visit during the holidays, look out for the festively festooned Holiday Train, which travels all the rail lines carrying (who else?) Santa.

Taste the Dog, Skip the Pizza

Did he really just suggest skipping the pizza, that classic deep-dish taste of Chicago? Of course not. Even thin-crust fanatics owe themselves a taste. But be sure to seek out the Chicago-style hot dog, too. The all-beef frankfurter is steamed to perfection before being stuffed into a fluffy bun and crowned with yellow mustard and a bevy of toppings, from white onions to pickled peppers to tomato slices. What a meal. Some of Chicago's vendors are as popular with locals as the wieners they sell, including Hot Doug's in Avondale and The Wiener's Circle in Lincoln Park.

Shop Lincoln Park, Skip Michigan Avenue

The shopping along Michigan Avenue is nothing short of legendary. But avid shoppers owe it to themselves to open their wallets along Armitage Avenue, Halsted Street and Webster Avenue in the Lincoln Park neighborhood. Dozens of shops cater to lovers of all things clothing, cosmetics, handbags, home décor, shoes, stationery and lingerie. Take a break and sip the daily drink specials at Kincade's. And enjoy the view: tree-lined streets and Victorian row houses make for a pretty setting.